2-(Dimethylamino)ethanol → HCID 23287779, compound

HRID 367040Notes

Reaction equation

HRID 367040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12](=[O:38])[O:13][C:14]([OH:37])([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:15]=2[CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:15]([CH2:16][C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[C:14]([O:37][CH2:42][CH2:41][N:40]([CH3:44])[CH3:39])([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[O:13][C:12]2=[O:38])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanol3×HCID 15895519HCID 15895519, compound

Product 1

HCID 23287779HCID 23287779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 125 mL dichloromethane was added 3-(3,5-Dimethoxy-phenyl)-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 5.0 g (9.57 mmol), giving a suspension. N,N-dimethylethanol-amine 2.66 g (29.8 mmol) was added, and the mixture was purged with anhydrous HCl gas until saturated. After an hour at room temperature, additional N,N-dimethyl-ethanolamine 1.33 g (14.9 mmol) was added, followed by stirring for 24 hours at room temperature. An additional N,N-dimethylethanolamine 2.66 g (29.8 mmol) was then added, followed by stirring for 24 hours at room temperature. The mixture was evaporated in vacuo, and the residue was suspended in ethyl ether. The ether suspension was washed exhaustively with 4 N NaOH, followed by water and saturated sodium chloride solution. The ether phase was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to a crude foam, 2.8 g. The crude material was purified by chromatography on 200 g silica gel eluted with 5% methanol in chloroform. The appropriate fractions were evaporated to a glassy solid, 2.31 g. The product was identified by 1H NMR, MS [M--H]+ =594.4 Da.

Workup

  1. customgiving a suspension
  2. customthe mixture was purged with anhydrous HCl gas until saturated
  3. waitAfter an hour at room temperature
  4. stirringby stirring for 24 hours at room temperature
  5. customThe mixture was evaporated in vacuo
  6. washThe ether suspension was washed exhaustively with 4 N NaOH
  7. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a crude foam, 2.8 g
  10. customThe crude material was purified by chromatography on 200 g silica gel
  11. washeluted with 5% methanol in chloroform
  12. customThe appropriate fractions were evaporated to a glassy solid, 2.31 g

Sources & evidence

ORD record
ord-993517a425f042fcbd37764230349ea3
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

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